Like many have already said, I was also a victim of the KC square-toed shoes, having owned a number of pairs a few years ago. But even worse were the piles of Express 1MX shirts...looking back I can't believe I ever wore those monstrosities. Terrible fit, even worse quality.... How they can claim those things are "modern fit" is beyond me.

I started lurking back in 2008 or so. Before that, I had a pair of black, rubber-soled, square-toed slipons that I bought just before heading to Japan, as I have larger feet and my first job here required me to dress "professionally" (though that was subject to a great degree of interpretation, judging by my coworkers). I knew nothing of rotation, but it's just as well: I wore them every day for 6 months, walking at least a couple miles each day, wearing through the soles and never having to touch them again afterward. I had to compromise on my next purchase due to a shortage of funds, finding a wide-fitting rubber-soled balmoral... But then I switched jobs to a better-paying one which didn't require a suit, so I've only worn them a few times since then. I might keep them for nostalgia even after the Aldens I ordered to replace then finally come in. I also have a pair of crappy chukkas that I bought in my "learning phase", when I was beginning to recognize good style, but still clueless about quality. The styling is right on, but the construction is cheap and I've already worn the backs of the heels up to the faux-leather lift, despite relatively limited wear. I'll get something better once they're no longer wearable, since they're comfortable and still look decent. I could regale you all with tales of my poor color-coordination skills as well, but alas, those are episodes I've mostly (willfully) forgotten.

Robert Talbot ties from Nordstroms. Before the great awakening, I used to load up with the most ungodly retna-burning silk you could imagine. Didn't want to be boring. Well, I sure wasn't that. Ended up throwing most of them out. The rest are for garden parties or some such. Or so I try to tell myself. I can't bear to wear them.

This thread delivers - but would be better with photographs of the offending garments.

Mine:

numerous ill-fitting suits

numerous colour-wheel fails

Ill-advised choices / colours e.g. cheap £150 Next suit; cheap £150 Next cream suit, complete with cheap £30ish duck-egg yellow loafers, a light pink shirt, and multi-striped lilac / lavender / pink tie - that get-up received 3 independents "Looking sharp!' comments, and the admiration of a rather attractive Canadian co-worker (being a complete beta-male, I utterly failed to even comprehend asking her on a date when I was talking to her back and forth at my previous company)

£550 on a no vent, flared (!) trousered MTM suit from Raja Fashions - I actually loved that suit, but I can get much more for my money and look better due my epiphany in discovering SF and learning about fit, fit and fit (best fit, then tailoring)

Usual square-toed monstrosities - and deluded in thinking that I was where it was at, baybee

Failure to understand shoe-rotation i.e. single pair of work shoes, single pair of casual shoes - wear out every 6 months, waste another £70 odd

SF unapproved but no regrets:

£100 on a pair of soft-leather burgundy derbies from Aldo - yes, I could spend a little more and get much better quality. However, I love the colour (even if it is wearing off at the toe crease), the SA provided me with good advice on shoes (discussed English brands e.g. Churches, Trickers) and introduced me to shoe-trees, shoe cream, and inadvertently, SF

I bought a few JAB suits about 3 or 4 years ago. I only paid $100 for them, and I got 2 shirts and 2 ties with each. Between the shirts, ties, and the pants from the suits, I still get use out of them, so I can't call the purchases complete wastes, but the jackets fit like crap. That, combined with SF, made me less confident in the knowledge of retail store employees.

PS: I bought those suits years ago, and I stopped wearing them years ago. I don't want anyone to think that I only recently realized the difference between clothes that do and don't fit well.

Mine are dress shirts with sleeves too short. And a Tommy Hilfiger suit that's too strong in the shoulders. I know TH gets dissed here a lot for low-quality, but the price was right and apart from the shoulders it looks good on me.